Building Pentagons into Graphenic Structures by On-Surface Polymerization and Aromatic Cyclodehydrogenation of Phenyl-Substituted Polycyclic Aromatic Hydrocarbons

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• 作者：Jia Liu ; Thomas Dienel ; Junzhi Liu ; Oliver Groening ; Jinming Cai ; Xinliang Feng ; Klaus Müllen ; Pascal Ruffieux ; Roman Fasel
• 刊名：Journal of Physical Chemistry C
• 出版年：2016
• 出版时间：August 11, 2016
• 年：2016
• 卷：120
• 期：31
• 页码：17588-17593
• 全文大小：484K
• 年卷期：0
• ISSN：1932-7455

文摘

Five-membered carbon rings play a crucial role in determining the geometric structures and electronic properties of carbon-based materials. However, incorporating five-membered rings into low-dimensional carbon nanomaterials with atomic precision is still a challenge. Here, we report on the on-surface synthesis of a one-dimensional conjugated polymer comprising fluoranthene subunits obtained by the surface-assisted aromatic cyclodehydrogenation of 1-phenylnaphthalene moieties within the precursor monomers. By using scanning tunneling microscopy (STM), we investigate the formation of the polymer by thermally induced dehalogenative aryl–aryl coupling and subsequent aromatic cyclodehydrogenation on a Au(111) substrate. The formed five-membered carbon rings are directly observed with atomic resolution by noncontact atomic force microscopy (nc-AFM). Our results show that carefully designed phenyl-substituted polycyclic aromatic hydrocarbons can be used for the rational fabrication of five-membered rings in the bottom-up synthesis of carbon-based nanomaterials and thus add a further tool to the emerging field of on-surface synthesis.